1-(1-icosyn-1-yl)-2-nitrobenzene | 1195790-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(1-icosyn-1-yl)-2-nitrobenzene
• CAS: 1195790-23-8
• 化学式: C₂₆H₄₁NO₂
• 分子量: 399.617
• InChiKey: OZQMYZQTMKRJGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  29.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  三乙基硅烷 、 1-(1-icosyn-1-yl)-2-nitrobenzene 在 platinum(IV) oxide 作用下， 反应 3.0h， 以85%的产率得到triethyl((E)-1-(2-nitrophenyl)icos-1-enyl)silane
  参考文献：
  名称：

  Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of fistulosin

  摘要：

  A synthetic route to 3-hydroxy-2-octadecylindole, the putative structure of the novel indole alkaloid fistulosin, starting from 2-nitro-1-iodobenzene was examined. Key steps include formation of a 1-stannyl-substituted 1-methoxy-1-alkene from a Fischer chromium carbene, intermolecular Kosugi-Migita-Stille coupling, and a palladium-catalyzed reductive N-heteroannulation. Demethylation of 3-methoxy-2-octadecylindole, a possible immediate precursor to 3-hydroxy-2-octadecylindole, was unsuccessful and gave instead methyl 2-(1-oxononadecanyl)aminobenzoate. The structure of the isolated alkaloid was suggested to be 2-(1-oxooctaclecanyl)aminobenzoate by comparison of analytical data with a synthetic sample. In addition. oxidation of 2-octadecylindole gave a 2,2'-dimer, a compound identical to previously prepared 3-hydroxy-2-octadecylindole. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.055
• 作为产物：
  描述：

  1-二十一碳炔 、 2-硝基碘苯 在 三乙胺 、 三苯基膦 、 palladium dichloride 、 copper(l) iodide 作用下， 反应 3.17h， 以95%的产率得到1-(1-icosyn-1-yl)-2-nitrobenzene
  参考文献：
  名称：

  Attempted synthesis of 3-hydroxy-2-octadecylindole. Proposed structural revision of previously prepared 3-hydroxy-2-octadecylindole and a proposed structure of fistulosin

  摘要：

  A synthetic route to 3-hydroxy-2-octadecylindole, the putative structure of the novel indole alkaloid fistulosin, starting from 2-nitro-1-iodobenzene was examined. Key steps include formation of a 1-stannyl-substituted 1-methoxy-1-alkene from a Fischer chromium carbene, intermolecular Kosugi-Migita-Stille coupling, and a palladium-catalyzed reductive N-heteroannulation. Demethylation of 3-methoxy-2-octadecylindole, a possible immediate precursor to 3-hydroxy-2-octadecylindole, was unsuccessful and gave instead methyl 2-(1-oxononadecanyl)aminobenzoate. The structure of the isolated alkaloid was suggested to be 2-(1-oxooctaclecanyl)aminobenzoate by comparison of analytical data with a synthetic sample. In addition. oxidation of 2-octadecylindole gave a 2,2'-dimer, a compound identical to previously prepared 3-hydroxy-2-octadecylindole. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.055